54483-84-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Dihydrocadambine is used as a pharmaceutical agent for its potential anti-inflammatory and antitumor effects. Its ability to modulate inflammatory responses and inhibit tumor growth makes it a promising candidate for the development of new medications to treat various diseases and conditions.
Used in Research Applications:
In the field of scientific research, 3-Dihydrocadambine serves as a subject of study for its potential pharmacological properties. Researchers are investigating its mechanisms of action, efficacy, and safety in order to better understand its potential applications and to develop new therapeutic strategies based on its unique characteristics.
Used in Traditional Medicine:
3-Dihydrocadambine may also be utilized in traditional medicine practices, where it could be employed for its purported health benefits. Its presence in the Psychotria tenuifolia plant may have been recognized for centuries, and it could be incorporated into herbal remedies and treatments that have been passed down through generations.

Upstream product

• 82958-43-8 (1S,4aS,8S,8aS)-8-{[2-(1H-Indol-3-yl)-ethylamino]-methyl}-6-methoxy-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester 
• 77988-08-0 (4S,5S,6S)-5-((S)-1,2-Dihydroxy-ethyl)-4-(2,2-dimethoxy-ethyl)-6-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 
• 82958-42-7 (1R,4aR,8S,8aR)-8-Formyl-6-methoxy-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester 
• 82958-41-6 (1R,4aR,8S,8aR)-8-Hydroxymethyl-6-methoxy-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Total Syntheses of (?)-Strictosidine and Related Indole Alkaloid Glycosides

A collective synthesis of glycosylated monoterpenoid indole alkaloids is reported. A highly diastereoselective Pictet–Spengler reaction with α-cyanotryptamine and secologanin tetraacetate as substrates, followed by a reductive decyanation reaction, was developed for the synthesis of (?)-strictosidine, which is an important intermediate in biosynthesis. This two-step chemical method was established as an alternative to the biosynthetically employed strictosidine synthase. Furthermore, after carrying out chemical and computational studies, a transition state for induction of diastereoselectivity in our newly discovered Pictet–Spengler reaction is proposed. Having achieved the first enantioselective total synthesis of (?)-strictosidine in just 10 steps, subsequent bioinspired transformations resulted in the concise total syntheses of (?)-strictosamide, (?)-neonaucleoside A, (?)-cymoside, and (?)-3α-dihydrocadambine.

The synthesis of 3α- and 3β-dihydrocadambine from secologanin

Secologanin, protected as the dimethyl acetal of its tetraacetate, had previously been dihydroxylated at the vinyl side chain with high stereoselectivity to provide the glycol (4) of the correct configuration for the synthesis of 3α- and 3β-dihydrocadambine.The glycol was converted to the cyclic acetal 5 to protect the secondary alcohol, the primary alcohol was oxidized to provide the aldehyde 7, and this was reductively coupled with tryptamine.Treatment of the coupled intermediate (8) with 90 percent formic acid followed by deacetylation of the glycoside led to the formation of a mixture of 3α- and 3β-dihydrocadambine (40 percent and 33 percent, respectively).The synthesis confirms the structure assigned to these alkaloids, and establishes the configuration, relative and absolute, at all centres except C-3 (where it provides no new stereochemical information).

A SYNTHESIS OF 3α-DIHYDROCADAMBINE

3α-Dihydrocadambine has been synthesized from secologanin.